YMMV / Road to Perdition

  • Acceptable Targets: The film is packed with enough Irish stereotypes to leave The Departed in the dust.
  • Adaptation Displacement: Many people don't even know the film is based on a graphic novel.
  • Complete Monster: In the novelization by Max Allan Collins, Harlen Maguire is a death-loving hitman who spends his free time photographing murders, many of which he himself perpetrates. Introduced killing a wounded man in a street alley, Maguire is then hired to track down Michael O'Sullivan and his son, Michael Jr., happily hoping to murder them both and add them to his massive "gallery of death". Slaughtering an entire cafe, murdering one of his own partners, and killing an innocent couple along the way, Maguire mortally wounds O'Sullivan and attempts to photograph his dying moments before moving onto Michael Jr., even after the contract on the duo has been called off.
  • Hilarious in Hindsight: Tyler Hoechlin's next role in a comic book adaptation was very different.
  • Magnificent Bastard: Frank Nitti.
  • Moral Event Horizon: Connor crosses it when he murders Michael Sr.'s wife and younger son, mistaking him for his older brother, just because he thinks the boy will rat him out.
  • Nightmare Fuel: Connor's murder of Annie and Peter. Adult Fear at its finest. The music doesn't make things better, particularly when Connor enters the room. Murder in Four Parts.
    • Blow-by-blow account: Michael Sr. frantically tries to call home, but the phone is off the hook. The camera cuts to Annie drying Peter off after a bath, then again to the upstairs hall. The bathroom door opens, and Connor enters, wearing a long coat and fedora, drawing a gun on mother and son. The camera moves back and forth between the pistol and Connor's eyes as Annie screams, then outside as Michael Jr. arrives home and sees two flashes inside his house, along with two gunshots. Getting off his bike, Michael Jr. sprints to the door... just as Connor reaches it. Michael Jr. freezes to the spot as Connor removes his hat and straightens his hair. Without seeing Michael, he opens the door, takes a swig from a flask, and leaves.
  • Tear Jerker: Who doesn't feel sorry for a little boy who's just lost his mom and little brother and is on the run from hitmen aiming to kill him and his father?
    • John Rooney's role in the end serves as this. He knows already that his son has been embezzling from him for years and it's hinted that Michael was closer family to him than Connor ever could be. However, despite realizing that Connor's death is imminent, he refuses to give him up, instead imploring for Michael to leave with his own son while he can. When Michael eventually returns to kill Rooney (as well as his entire entourage), the old man can only solemnly remark that he's glad that Michael would be the one to kill him.
    • The film was the final film appearance of Paul Newman (not including his voice-only acting which came after), making this a Meta Tear-Jerker in Hindsight.